Recent advances of diaryl ether family as HIV-1 non-nucleoside reverse transcriptase inhibitors

Current Pharmaceutical Design

Volumn 19, Issue 15, 2013, Pages 2829-2838

  Chen, Xuwang ^a   Ding, Shufang ^a   Zhan, Peng ^a   Liu, Xinyong ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Diaryl ether; Drug design; HIV 1; MK 4965; Molecular simulation; NNRTIs

Indexed keywords

BENZOPHENONE; DELAVIRDINE; DIARYL ETHER; EFAVIRENZ; ETHER; ETRAVIRINE; MK 4965; NEVIRAPINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PYRIDAZINONE DERIVATIVE; RILPIVIRINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PHASE 2 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VIRUS STRAIN;

ANTI-HIV AGENTS; HIV REVERSE TRANSCRIPTASE; HUMANS; MODELS, MOLECULAR; REVERSE TRANSCRIPTASE INHIBITORS;

EID: 84876698854     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319150018     Document Type: Article

References (44)

1. WHO/UNAIDS. Global AIDS report. 2011.
2. Mehellou Y, De Clercq E. Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J Med Chem 2010; 53: 521-38.
3. Panos G, Samonis G, Alexiou VG, et al. Mortality and morbidity of HIV infected patients receiving HAART: a cohort study. Curr HIV Res 2008; 6: 257-60.
4. de Bethune MP. Non-nucleoside reverse transcriptase inhibitors (NNRTIs), their discovery, development, and use in the treatment the last 20 years (1989-2009). Antiviral Res 2010; 85: 75-90.
5. Chen XW, Zhan P, Li DY, et al. Recent Advances in DAPYs and Related Analogues as HIV-1 NNRTIs. Current Medicinal Chemistry 2011; 18: 359-76.
6. De Clercq E. The design of drugs for HIV and HCV. Nat Rev Drug Discov 2007; 6: 1001-18.
7. Sax PE. FDA approval: etravirine. AIDS Clin Care 2008; 20: 17-8.
8. Tucker TJ, Saggar S, Sisko JT, et al. The design and synthesis of diaryl ether second generation HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) with enhanced potency versus key clinical mutations. Bioorg Med Chem Lett 2008; 18: 2959-66.
9. Orr DC, Figueiredo HT, Mo CL, et al. DNA chain termination activity and inhibition of human immunodeficiency virus reverse transcriptase by carbocyclic 2',3'-didehydro-2',3'-dideoxyguanosine triphosphate. J Biol Chem 1992; 267: 4177-82.
10. Wyatt PG, Bethell RC, Cammack N, et al. Benzophenone derivatives: a novel series of potent and selective inhibitors of human immunodeficiency virus type 1 reverse transcriptase. J Med Chem 1995; 38: 1657-65.
11. Chan JH, Freeman GA, Tidwell JH, et al. Novel benzophenones as non-nucleoside reverse transcriptase inhibitors of HIV-1. J Med Chem 2004; 47: 1175-82.
12. Romines KR, Freeman GA, Schaller LT, et al. Structure-activity relationship studies of novel benzophenones leading to the discovery of a potent, next generation HIV nonnucleoside reverse transcriptase inhibitor. J Med Chem 2006; 49: 727-39.
13. Ferris RG, Hazen RJ, Roberts GB, et al. Antiviral activity of GW678248, a novel benzophenone nonnucleoside reverse transcriptase inhibitor. Antimicrob Agents Chemother 2005; 49: 4046-51.
14. Ren J, Chamberlain PP, Stamp A, et al. Structural basis for the improved drug resistance profile of new generation benzophenone non-nucleoside HIV-1 reverse transcriptase inhibitors. J Med Chem 2008; 51: 5000-8.
15. Wang Z, Wu B, Kuhen KL, et al. Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 2006; 16: 4174-7.
16. De La Rosa M, Kim HW, Gunic E, et al. Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2006; 16: 4444-9.
17. Muraglia E, Kinzel OD, Laufer R, et al. Tetrazole thioacetanilides: potent non-nucleoside inhibitors of WT HIV reverse transcriptase and its K103N mutant. Bioorg Med Chem Lett 2006; 16: 2748-52.
18. Girardet JL, Koh YH, Rosa HMDL, et al. S-triazolyl amercaptoacetanildes as inhibitors of HIV reverse transcriptase. World Patent WO 2006026356 A2. 2006 Mar.
19. Koch U, Kinzel O, Muraglia E, et al. HIV reverse transcriptase inhibitors. World Patent WO 2006037468 A1. 2006 Apr.
20. Gagnon A, Landry S, Coulombe R, et al. Investigation on the role of the tetrazole in the binding of thiotetrazolylacetanilides with HIV-1 wild type and K103N/Y181C double mutant reverse transcriptases. Bioorg Med Chem Lett 2009; 19: 1199-205.
21. Sweeney ZK, Klumpp K. Improving non-nucleoside reverse transcriptase inhibitors for first-line treatment of HIV infection: the development pipeline and recent clinical data. Curr Opin Drug Discov Devel 2008; 11: 458-70.
22. Moyle G, Boffito M, Stoehr A, et al. Phase 2a randomized controlled trial of short-term activity, safety, and pharmacokinetics of a novel nonnucleoside reverse transcriptase inhibitor, RDEA806, in HIV-1-positive, antiretroviral-naive subjects. Antimicrob Agents Chemother 2010; 54: 3170-8.
23. Zhan P, Li Z, Liu X, et al. Sulfanyltriazole/tetrazoles: a promising class of HIV-1 NNRTIs. Mini Rev Med Chem 2009; 9: 1014-23.
24. O'Meara JA, Jakalian A, LaPlante S, et al. Scaffold hopping in the rational design of novel HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 2007; 17: 3362-6.
25. Gagnon A, Amad MH, Bonneau PR, et al. Thiotetrazole alkynylacetanilides as potent and bioavailable non-nucleoside inhibitors of the HIV-1 wild type and K103N/Y181C double mutant reverse transcriptases. Bioorg Med Chem Lett 2007; 17: 4437-41.
26. Tucker TJ, Sisko JT, Tynebor RM, et al. Discovery of 3-{5-[(6- amino-1H-pyrazolo[3,4-b]pyridine-3-yl)methoxy]-2- chlorophenoxy}-5 -chlorobenzonitrile (MK-4965): a potent, orally bioavailable HIV-1 non-nucleoside reverse transcriptase inhibitor with improved potency against key mutant viruses. J Med Chem 2008; 51: 6503-11.
27. La Regina G, Coluccia A, Silvestri R. Looking for an active conformation of the future HIV type-1 non-nucleoside reverse transcriptase inhibitors. Antivir Chem Chemother 2010; 20: 213-37.
28. Tucker TJ, Tynebor R, Sisko JT, et al. Non-nucleoside reverse transcriptase inhibitors. World Patent WO 2009067166 A2. 2009 May.
29. Arora N, Billedeau RJ, Kennedy-Smith J, et al. Inhibitors of HIV-1 reverse transcriptase. United States patent US 2010056535 A1. 2010 Mar.
30. Gomez R, Jolly SJ, Williams T, et al. Design and synthesis of conformationally constrained inhibitors of non-nucleoside reverse transcriptase. J Med Chem 2011; 54: 7920-33.
31. Sweeney ZK, Acharya S, Briggs A, et al. Discovery of triazolinone non-nucleoside inhibitors of HIV reverse transcriptase. Bioorg Med Chem Lett 2008; 18: 4348-51.
32. Sweeney ZK, Kennedy-Smith JJ, Wu J, et al. Diphenyl ether nonnucleoside reverse transcriptase inhibitors with excellent potency against resistant mutant viruses and promising pharmacokinetic properties. ChemMedChem 2009; 4: 88-99.
33. Sweeney ZK, Welch M. Non-nucleoside reverse transcriptase inhibitors. World Patent WO 2008119662 A1. 2008 Oct.
34. Kennedy-Smith J, Sweeney ZK, Wu J. Non-nucleoside reverse transcriptase inhibitors. World Patent WO 2008145562 A1. 2008 Dec.
35. Peat AJ, Sebahar PR, Youngman M, et al. Chemical compounds. World Patent WO 2008154271 A1. 2008 Dec.
36. Sweeney ZK, Dunn JP, Li Y, et al. Discovery and optimization of pyridazinone non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2008; 18: 4352-4.
37. Elworthy TR, Dunn JP, Hogg JH, et al. Orally bioavailable prodrugs of a BCS class 2 molecule, an inhibitor of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2008; 18: 6344-7.
38. Saito YD, Smith M, Sweeney ZK. Non-nucleoside reverse transcriptase inhibitors. United States patent US 2007078128 A1. 2007 Apr.
39. Sweeney ZK, Harris SF, Arora SF, et al. Design of annulated pyrazoles as inhibitors of HIV-1 reverse transcriptase. J Med Chem 2008; 51: 7449-58.
40. Su DS, Lim JJ, Tinney E, et al. Biaryl ethers as novel nonnucleoside reverse transcriptase inhibitors with improved potency against key mutant viruses. J Med Chem 2009; 52: 7163-9.
41. Elworthy TR, Hogg JH, Kennedy-Smith J, et al. Urea and carbamate derivatives as non-nucleoside reverse transcriptase inhibitors. World Patent WO 2009000663 A1. 2008 Dec.
42. Su DS, Lim JJ, Tinney E, et al. Biaryl ethers as potent allosteric inhibitors of reverse transcriptase and its key mutant viruses: aryl substituted pyrazole as a surrogate for the pyrazolopyridine motif. Bioorg Med Chem Lett 2010; 20: 4328-32.
43. Aquino CJ, Dickson H, Peat AJ. Chemical compounds. World Patent WO 2008157273 A1. 2008 Dec.
44. Aquino CJ, Dickson H, Peat AJ. Chemical compounds. World Patent WO 2008157330 A1. 2008 Dec.